ChemicalBook CAS DataBase List p-Mentha-1(6),8-diene-4-ol

p-Mentha-1(6),8-diene-4-ol synthesis

10synthesis methods

Product Name:p-Mentha-1(6),8-diene-4-ol
CAS Number:3419-02-1
Molecular formula:C10H16O
Molecular Weight:152.23

2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene

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Yield: 74.4% ， 8.3%

Reaction Conditions:

with hydrogen in ethyl acetate at 25 - 125; under 3750.38 Torr; for 24 h;Autoclave;Inert atmosphere;Overall yield = 82.7 %;Temperature;Reagent/catalyst;Solvent;Time;

Steps:

2 Isomerization/hydrogenation with copper chromite catalyst, barium promoted (Product No. AB120210, CAS no. 12018-10-9, from ABCR GmbH, Karlsruhe, Germany) in ethyl acetate (125°C, 50% terpinolene epoxide in ethyl acetate)
32 g (0.204 mol) terpinolene epoxide (97.1 %), 32 g (0.363 mol) ethyl acetate and 0.918 g (0.004 mol) copper chromite (CuCr₂0₄, barium promoted, Product No. AB120210, CAS no. 12018-10-9, from ABCR GmbH, Karlsruhe, Germany) were charged into an autoclave under nitrogen atmosphere. The mixture was pressurized with 5 bar H2 and then heated to 125°C under vigorous stirring. The mixture was stirred for 24 h at 125°C and then cooled to 25°C. The pressure was released and the catalyst was filtered off through a layer of diatomaceous earth. The remaining catalyst was washed with ethyl acetate (5 g). Filtrate and wash ethyl acetate were combined and ethyl acetate was distilled off at reduced pressure (distillation residue: 30.7 g). Quantitative GC (GC with internal standard) of the distillation residue showed a limonene-4-ol concentration of 75.33% and a terpinene-4-ol concentration of 8.51 %. This corresponds to a yield of 74.4% for limonene-4-ol and 8.3% for terpinene-4-ol. Total yield of limonene-4-ol and terpinene-4-ol was 82.7%.

References:

BASF AGRO B.V.;WOLF, Bernd;RACK, Michael;BENSON, Stefan;GOETZ, Roland;KRAUS, Helmut WO2017/144337, 2017, A1 Location in patent:Page/Page column 13

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References

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1195-32-0 Synthesis